The Lessons Hidden in the Peaks and Valleys

For all my fellow business owners and entrepreneurs—how many times a day do you question your choices?

I would say at least once a day I find myself thinking about why I chose the path of working for myself and starting my own event business. Working with corporate clients, sometimes I see their day-to-day and think, wow, the grass really does look greener over there. All the memes about trading traditional 40-hour work weeks for “flexibility” that somehow turns into 80-hour weeks feel a little too real (not including the guaranteed 4–6 hours of tossing and turning that hit at some point during the week as you stress about an email, a decision, or spiral about whether you’re doing

anything correctly when running your business).

I constantly laugh at myself and how I exchanged conference calls at a desk during normal business hours for pacing in front of a random lamppost in Disney World while my family waits for me to “wrap it up.” Things you give up when you choose this road include stress-free vacations (or really, formal vacation days at all), the ability to escalate an issue to your manager (sorry, that’s you), and built-in promotions, raises, and bonuses.

But of course, we chose this for a reason.

We ignored all of that because the moments of pride, satisfaction, and beaming self-esteem are addicting. Especially if you’re in the events world—not all industries offer a space where you get to see projects come to fruition. Happy guests, beaming clients, and being in the trenches with your fellow vendors bring a joy that’s indescribable. Of course, the ability to “choose your hours,” not report into anyone, and feel in control of your destiny are additional perks—but it’s the successes, and whatever we define as “wins,” that truly hook us.

It’s taken a lot of learning for me to realize that every “win” and every “failure” is pointing me in some direction. I am the first to say I’m an emotional person. When I first started my business, I felt every single success and failure deeply. Why wouldn’t I? My name is on it, and everything felt like a personal reflection of me.

I quickly (depending on how you define “quickly”) realized I wasn’t going to sustain this. I needed to find a way to approach each turn differently—still learning from what didn’t work out and celebrating what did.

With the help of countless podcasts, books, and conversations with peers, I’ve learned to reframe it all as signs pointing me and my business in the right direction. Not in a “woo-woo” way—but in a practical sense: if you allow yourself to learn from both the challenges and the moments that bring you joy, you’ll naturally move toward the right path.

An important part of this realization is understanding that what you initially saw as the end goal—or put on your vision board—may not be where you end up. You might end up somewhere bigger, better, or simply healthier for you.

This can be one of the hardest parts of being an entrepreneur, especially in a world full of imposter syndrome fueled by curated social media. The ability to let go and trust the process requires vulnerability, humility, and a willingness to go with the flow. I’m about as Type A as they come, so this wasn’t exactly in my natural vocabulary—but I’ve grown to appreciate how things unfold in my business. It takes the pressure off feeling like I need to have all the answers and instead allows me to focus on making decisions that feel authentic to me, my experience, and what I want for my business.

I’ve run my business for over 8 years, and it’s taken nearly all of that time (with subtle reminders along the way) to fully embrace this mindset. So I’m not expecting you to read this and suddenly shift your perspective—but I do encourage you to look back at your own peaks and valleys and consider how they may have been guiding you.

I’ll share a few of mine to get you started:

• I used to equate success with having an office space. And honestly, I think others did too—because as soon as I had one, it felt like people took me more seriously. We had our space for two years, and it served its purpose. Eventually, I realized I was rarely there, clients were mostly meeting via Zoom, and when we did meet in person, the location didn’t really matter. While I loved having it as a landing pad, storage space, and legitimizer, the cost ultimately outweighed the benefits. Not to mention, the “work from anywhere” perk started to feel restrictive when I had an office I felt guilty not using. Maybe someday we’ll have a brick-and-mortar again—but for now, I prefer my 30-second commute to the living room.

  
  

• I started in corporate events and never thought weddings would be part of my work. But as my friends reached the age of getting married, I kept hearing, “You’re an event planner—can you help my friend with her wedding?” Knowing I eventually wanted to go out on my own, I took the opportunity and grew to love it. I worked part-time with another wedding planner and learned as much as I could. When I launched my own business, I knew weddings had to be part of our portfolio. I loved working closely with couples and their families, designing meaningful experiences, and watching everyone hit the dance floor at the end of the night. When COVID hit in 2020, weddings—though very different—were the only events still happening. Without that part of my business, I’m not sure I would have made it through. It truly sustained me. Not to mention, I’ve met some of my best “friendors” through weddings.

  
  

• Other quick hits that resonate:

  • The difficult clients who teach you boundaries and better contract clauses

  • The events that may not be glamorous but consistently generate leads

  • The team members who show you exactly what you do—and don’t—want in a team

  • The moments of burnout that force you to admit something isn’t working

  • The wins that had nothing to do with you—because you built the right team

  • Hearing client feedback that mirrors your internal mission statement, reminding you you’re on the right track

    
    

This post is just as much a reminder to myself to embrace the peaks and valleys as it is something I learned the hard way that I hope resonates with someone else building their business.

Some lessons we learn once and never forget. Others require the universe to keep reminding us which path we’re on.