What happens when someone you’ve worked with for years decides it’s time to leave?

When a longtime member of Drew’s team decides to go out on his own, it brings up a bigger question: Should your team really feel like family?

In this episode of Get Over It, Drew and Heidi talk about the complicated relationship between leadership, loyalty, and letting people grow. They get into why an employee leaving can feel so personal, how leaders can become overly responsible for the people they work with, and why someone choosing a new path doesn’t necessarily mean something went wrong.

Heidi shares her own experiences with longtime team members moving on and what she’s learned from working alongside her daughter, while Drew wrestles with the realization that sometimes a great leader’s job isn’t to keep people, it’s to help them grow, even if that growth eventually takes them somewhere else.

They also dig into workplace boundaries, different communication styles, showing appreciation in ways people actually value, the danger of creating “golden handcuffs,” and why putting relationships first doesn’t mean avoiding the hard conversations.

In This Episode, Drew & Heidi Discuss:

• Should your team really feel like family?
• Why an employee leaving can feel like a personal betrayal
• How leaders can separate someone else’s decision from their own self-worth
• Leading people without taking responsibility for every part of their success
• Working with actual family in a family business
• Understanding how different team members communicate and process conflict
• Why great employees sometimes outgrow their roles
• The difference between helping people stay and making them feel trapped
• Creating healthy boundaries between relationships and business
• Why strong workplace relationships still require honesty and accountability
• Learning to let people grow, even when that means letting them go

Because maybe the goal of great leadership isn’t to build a team that never leaves.

Maybe it’s to build people who are capable of choosing what comes next.

🎙️ Listen to Get Over It wherever you get your podcasts, and send this episode to a leader, business owner, or teammate who needs to hear this conversation.

Are you actually preparing… or are you just avoiding the thing that scares you?

In this episode of Get Over It, Drew admits something he almost didn’t want to say out loud: he almost didn’t show up to record. At first, he thought the problem was a lack of structure. He needed a better plan, a clearer direction, more time to prepare.

Then he realized what was really going on, he was scared.

That confession opens up a candid conversation with Heidi about fear, perfectionism, imposter syndrome, and the ways high performers can disguise avoidance as productivity. They unpack why planning can be both a strength and a trap, what happens when you don't feel qualified to be in the room, and why taking action is often the only way to break the loop.

They also explore the importance of having people in your life who are willing to call you out, the difference between commitments we make to others and the ones we make to ourselves, and why admitting you're afraid might be exactly what helps you move forward.

If you've ever told yourself you need to learn a little more, plan a little longer, or get everything perfectly in place before you start, this episode might make you ask:

Are you getting ready… or just getting ready to get ready?

• How fear can disguise itself as planning and preparation
• Why high performers struggle to admit when they're scared
• Imposter syndrome and questioning whether you belong in the room
• When planning goes from a strength to a form of procrastination
• Why perfection can keep you from taking action
• The power of having people who are willing to call you out
• Using education and experience to build confidence
• Why accountability to others can feel stronger than accountability to yourself
• Recognizing the stories you tell yourself when you're avoiding something
• How awareness + action can help break the cycle

Sometimes you don't need another plan.

Sometimes you just need to admit you're scared, and do it anyway.

🎙️ Listen to Get Over It wherever you get your podcasts, and share this episode with someone who's been getting ready to get ready.

In This Episode, Drew & Heidi Discuss:

Are you driven by ambition... or by fear?

In this episode of Get Over It, Drew and Heidi dive into one of the biggest questions facing high achievers: When does healthy ambition become hustle fueled by fear?

From chasing career goals and financial success to navigating relationships, self-worth, and even social media, they explore the hidden pressure of feeling like you're never doing enough—or that you are never enough.

Together, they unpack the difference between measurable growth and the internal stories we tell ourselves, why so many of us tie our worth to productivity, and how learning to define "enough" for ourselves can lead to greater peace, healthier relationships, and a more fulfilling life.

If you've ever struggled to slow down, felt guilty for resting, or wondered why success never seems to feel like enough, this conversation is for you.

In This Episode, Drew & Heidi Discuss:

• The difference between healthy ambition and fear-driven hustle
• Why high performers often believe they're never doing enough
• The connection between productivity, self-worth, and shame
• How childhood experiences shape our relationship with success
• Why rest can feel uncomfortable—even when we desperately need it
• The hidden cost of chasing "more" in work, money, and relationships
• Defining what "enough" looks like in different areas of life
• How clarity can replace the constant pressure to achieve

Practical questions to help you recognize when you're hustling from fear instead of purpose

Key Takeaways

• "Enough isn't a number—it's a decision."
• "Healthy ambition moves you forward. Fear convinces you you'll never arrive."
• "Rest isn't something you earn. It's what allows you to keep growing."
• "The standard you live by should be yours—not someone else's."

Why do we keep saying yes... even when we know our plate is already full?

In this episode of Get Over It, Drew and Heidi have an honest conversation about overcommitting, burnout, people-pleasing, and the pressure to do it all. From growing businesses and maintaining relationships to protecting personal time, they unpack why high achievers often struggle to say no—and the hidden cost that comes with always saying yes.

Together, they explore how overcommitment impacts mental health, relationships, business, and even the things that bring us the most joy. They also share practical questions you can ask yourself before taking on another responsibility, helping you create healthier boundaries without guilt.

If you've ever felt stretched too thin, constantly busy, or like you're chasing the next thing instead of enjoying the life you've built, this conversation is for you.

In this episode, Drew and Heidi discuss:

• Why high performers tend to overcommit
• The connection between busyness, productivity, and self-worth
• How saying yes too often can lead to burnout
• Why the things that bring us the most joy are often the first to disappear when life gets busy
• Learning that "no" is a complete sentence
• The hidden costs of overcommitting in business and personal relationships
• Why awareness is the first step toward creating healthier boundaries
• A simple decision-making filter to help determine when to say yes—and when to say no
• How staying connected to the people who matter most can become your compass for making better decisions

• "Overcommitment isn't always productivity."
• "Busy doesn't always mean you're moving closer to the life you want."
• "The things that fill your cup shouldn't be the first things you cancel."
• "Sometimes overcommitment is really an addiction to distraction."
• "Before saying yes, ask yourself: Is this bringing me closer to where I want to be—or pulling me further away?"

• Creating healthy boundaries
• Building sustainable habits
• Prioritizing relationships over constant productivity
• Evaluating commitments through a long-term lens

Have you ever found yourself saying yes when you really wanted to say no?

Leave a review, share this episode with someone who needs to hear it, and let us know what topic you'd like us to Get Over It next.

In this episode, Drew and Heidi talk about AI — the good, the bad, and the strange reality of how quickly people are starting to rely on it for everything.

They get into the growing belief that access to information automatically creates expertise, and how AI can sometimes create a false sense of confidence without real understanding or experience behind it. From business decisions to personal relationships, they unpack what happens when people stop thinking critically and start outsourcing too much of their judgment.

The conversation also explores authenticity, communication, and the tension between using AI as a tool versus letting it replace real human connection. They share their own experiences using it, where it’s helpful, where it falls short, and why intention still matters more than technology.

At the end of the day, AI can help organize information — but it can’t replace experience, discernment, or the heart behind the message.

In this episode, Drew and Heidi talk about burnout — what it actually feels like, how it sneaks up on you, and the stories we start telling ourselves when we’ve been pouring into everyone else for too long.

They get into the emotional exhaustion that can come from constantly showing up for people, the pressure of always being “on,” and what happens when you start feeling unappreciated or disconnected from the very things that once gave you energy.

The conversation also explores the difference between needing rest versus trying to emotionally detach, and how pulling away from relationships, people, or purpose can sometimes make burnout even worse.

From business to personal relationships, Drew and Heidi unpack what burnout has looked like in their own lives, how they’ve navigated it, and what it takes to reconnect with yourself when you’ve hit a wall.

At the end of the day, burnout isn’t always about doing too much — sometimes it’s about losing connection to the things that once made you feel alive.

In this episode, Drew and Heidi talk about appearance and why it matters — whether we want it to or not.

They get into how quickly first impressions are formed, and how the way you show up can influence how people perceive you in both business and everyday interactions. From real-life scenarios to personal habits, they unpack how appearance ties directly to confidence, energy, and presence.

They also talk about the connection between how you look and how you feel, and how being intentional about how you present yourself can change the way you move through your day.

At the end of the day, it’s not about perfection — it’s about understanding the role it plays and deciding how you want to show up.

In this episode, Drew and Heidi talk about self-care — not the version that looks good on the surface, but the kind that actually keeps you functioning when life and business start to get heavy.

As schedules fill up and demands increase, the first thing most people drop is themselves. They get into the difference between maintenance and real self-care, why it’s often the first thing to go, and what happens when you stop taking care of the basics.

They share how small, consistent habits — like movement, sleep, and routine — directly impact how you show up in your business and your life, and why waiting to “fit it in later” usually means it doesn’t happen at all.

At the end of the day, it’s not about doing it perfectly — it’s about recognizing when you’ve fallen off and deciding to get back to what works.

In this episode, Drew and Heidi talk about why we avoid difficult conversations — not because we don’t know what to say, but because we’re afraid of what might happen if we do.

Whether it’s with clients, team members, friends, or even the people closest to us, avoiding the conversation doesn’t make the situation better — it usually makes it worse. They share real examples from business, leadership, and personal life, and what changed when they finally said the thing they were avoiding.

They talk about the fear of being judged, the tendency to delay, and how not having the conversation can actually do more harm than having it. From price reductions to team performance to marriage and finances, the common thread is simple — telling the truth moves things forward.

At the end of the day, it’s not about having the perfect words — it’s about having the conversation.

In this episode, Drew and Heidi talk about what you’re feeding your mind versus what you’re allowing in — and how both shape how you show up when things get hard.

Your mind is constantly taking in something — whether you’re paying attention to it or not.

Drew leans into the idea of feeding your mind with better inputs — podcasts, conversations, and perspective — while Heidi focuses on protecting it by being intentional about what (and who) gets access in the first place.

They talk about why your environment and associations matter more than you think, how small inputs can shift your mindset quickly, and what to do when you feel off.

At the end of the day, it’s not about being perfect — it’s about recognizing what’s getting in and deciding what to do about it.