It’s All Going to Work Out: Real Lessons from Women Who’ve Been There

What would you tell your younger self if you could go back in time? That everything will work out? To stop stressing over what others think? That it's okay not to have all the answers, or even a plan?

On the Checking Inn podcast, we engage in thoughtful conversations with industry professionals, educators, and entrepreneurs to explore hospitality and tourism challenges, opportunities, and adventures (as well as some crab cake and bean pie debate). 

At the end of each show, we ask our guest:“If you could go back in time, what would you tell your 20-year-old self?”

The responses from women across the hospitality industry have been honest, funny, moving—and deeply insightful. From CEOs and senior executives like Rachelle Peterson (LOQIA Group), Tracy Prigmore (She Has a Deal), and Anna Blue (American Hotel & Lodging Foundation) to leading educators such as Dr. Berkita Bradford, Lisa Cain, and Michelle Russen, the collective wisdom spans every corner of the industry.

We’ve heard from leaders at Marriott and Hilton, revenue experts like Karen Ramon (Sonesta Hotels), legal voices such as Carolyn D. Richmond (NYC Hospitality Alliance), content experts like Seema Jain (Seva Global) and Ashli Johnson (Hospitality Hued), and entrepreneurs and media leaders—including hertelier's own Emily Goldfischer. Students and recent graduates have shared their perspectives too, creating a rich mosaic of insights from all levels of the field.

Whether you're just getting started, contemplating a pivot, or simply looking for a boost of encouragement, these reflections offer perspective, courage, and reminders that you're not alone. Here are eight key themes that emerged—each one a nudge toward growth, confidence, and clarity.

Whether you’re just getting started, contemplating a pivot, or somewhere in between, their wisdom will likely feel familiar. Here are eight themes that emerged, each offering a gentle nudge, a dose of courage, and the kind of perspective that only comes from experience.

Self-Awareness & Confidence: Own Who You Are

For many women in hospitality, confidence isn’t something you’re born with. It’s something you build, day by day, shift by shift, mistake by mistake. And it starts with self-awareness.

• “Nobody has the answer. Ask questions, be confident in who you are.”

This quote says it all: leadership isn’t about always being right. It’s about being curious, showing up with humility, and standing firm in your identity even when you’re learning.

• “Follow my confidence instead of my fear.”

• “Confidence comes from knowing who you are and knowing how to push yourself and when to settle in and be where your feet are.”

  
  

The hospitality industry can be intense. You’re navigating long hours, high stakes, and often, emotionally charged environments. In this context, learning when to stretch, and when to ground yourself, is a key part of building confidence.

But confidence also comes from letting go of outside judgment.

• “Stop worrying about what other people think.”

• “Know your worth. What you’re doing is valuable.”

• “You are amazing and will get through this.”

• “Advocate for yourself.”

• “Get comfortable being uncomfortable.”
  

Confidence isn’t just about projecting strength. Sometimes, it looks like raising your hand when you’re unsure, saying no when a boundary is crossed, or simply showing up to the next challenge despite the butterflies in your stomach. That’s what real growth looks like.

Trusting Yourself & Following Your Heart

Hospitality isn’t a one-size-fits-all career. It’s a journey filled with twists, pivots, and gut decisions. That’s why so many women shared advice about listening to their inner voice.

• “Follow your heart and your gut.”

• “Follow your gut, and stop comparing yourself to others.”

• “As long as you continue to follow your heart and continue to do what you love, and don’t see the connection, keep going—it’ll all end up the way it’s supposed to be.”

  
  

We often hear the phrase “trust the process,” but trusting yourself, especially when things aren’t going smoothly, takes real courage. It’s easy to second-guess or compare paths, especially in an industry where promotions, travel, and high-profile roles can feel like the only measures of success.

• “Don’t let fear of change stop you from doing something different, out of your comfort zone.”

• “Anything you want is possible, but you must make the dream happen.”

  
  

It’s not just about passion; it’s about persistence. Trusting your heart doesn’t mean the road will be easy, it means you’ll be anchored to something real when things get hard. And they will. But if you keep moving forward with integrity, the right path will start to unfold.

Letting Go, Self-Care & Acceptance

There’s a reason so many women echoed this one phrase:

• “It’s all going to work out.”
  

It might not happen on your timeline. It might not look the way you expected. But you will survive, and probably come out stronger. That’s why letting go – of perfectionism, of overcommitment, of comparison – is essential.

• “Self-care. Everything will be okay.”

• “Don’t worry about it, it’ll all work out fine.”

• “Relax! Live in the moment. It all works out. It’s a steppingstone.”

• “Everything will be okay. Life is full of challenges.”

• “It’s going to be okay.”

  
  

Hospitality professionals are often known for their “yes” attitude. But the women who’ve made it far also learned how to say “no.”

• “You will drive yourself crazy if you take on everything. Choose your battles.”
  

Self-care isn’t indulgent, it’s strategic. It’s how you maintain longevity in an industry known for burnout. You can’t give your best to guests, teams, or partners if you’re constantly running on empty. And guess what? The world won’t fall apart if you take a break.

Listening, Learning & Growth

Some of the most moving advice had less to do with ambition and more to do with humility.

• “Be a better listener in all aspects of life. Ask more questions. Learn to listen.”

Hospitality is about people. The best professionals know how to read a room, pick up on what’s not being said, and make someone feel seen, whether that’s a guest, a colleague, or themselves. That kind of emotional intelligence starts with listening.

• “I love you, appreciate you. Thank you. Without the lessons and mistakes I wouldn’t be where I am now.”

  
  

That level of grace doesn’t come easy. It’s forged through setbacks, awkward conversations, and learning to own your missteps. But it pays off.

• “The fight will not be easy, but worth it.”
  

Growth doesn’t always come with a certificate or promotion. Sometimes, it’s reflected in how we respond to criticism, navigate conflict, or support others coming up behind us. Listening, really listening, is one of the most generous acts of leadership.

Advice & Direction: Say Yes, Do It Now

Some advice was refreshingly direct: short, sweet, and powerful.

• “Do it now!”

• “Say yes to more things.”

• “Put yourself out there.”

  
  

You can feel the urgency in these statements: the awareness that time is precious, and that waiting for perfection often leads to missed opportunities.

• “Don’t compare yourself to others. Whatever you do, make sure it’s to never hurt anyone and to better yourself.”

• “Don’t have your life be your job.”

• “It is never too late.”
  

Whether it’s applying for a leadership program, pitching a new concept, or taking a chance on a new city or role, these women want you to know: you don’t have to wait for permission.

It’s okay to take up space. It’s okay to pivot. And if you’re not happy where you are? It’s never too late to start again.

Career & Financial Wisdom: Think Long-Term

Many women also shared advice that was practical: 

• “Enjoy the industry. Fun to be had within the industry.”

• “Buy real estate. Start investing early on.”

• “Whatever you choose, have passion for it. Even if it’s considered taking a step backwards.”
  

This advice may feel unexpected, but it reflects a deep truth: stability and joy in your career often require strategic choices. The hospitality industry can be unpredictable, and thinking ahead – about money, time, and lifestyle – creates more room for freedom later.

Whether it’s negotiating for a better salary, saving early, or learning how to read a profit & loss statement, financial literacy is a feminist issue. It empowers women to make choices based on their goals, not just survival.

And passion? That matters too.

• “Whatever you choose, have passion for it.”
  

Even if it means making a less conventional move. Especially if it does.

Passion & Purpose: Keep Going

In an industry driven by service, it’s easy to lose sight of why you started. That’s why so many women returned to the theme of passion – not in a romanticized way, but in a grounded, deeply personal sense.

• “Keep chasing your passion.”

  
  

When the work gets repetitive or exhausting, when the culture isn’t inclusive, when you're not sure if it’s still worth it, these are the moments when purpose can carry you through.

Sometimes that means staying the course. Other times, it means rerouting. But either way, returning to what drives you is how you prevent burnout, how you build resilience, and how you keep showing up in meaningful ways.

Final Thoughts: “It’s All Going to Work Out”

If there’s one message threaded throughout every quote, it’s this:

• “It’s all going to work out.”

  
  

It doesn’t mean there won’t be bumps. It doesn’t mean you’ll never feel stuck, frustrated, or behind. But it does mean you’re stronger than you think, and that most of the time, you're doing just fine.

So whether you're making coffee, managing a resort, or leading a brand into the future, know this: you’re not alone. Thousands of women have walked this path before you. And they’re rooting for you now.

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