What My Wedding Taught Me About Running a Successful Business

strategic planning Aug 08, 2023

With my wedding anniversary approaching, I've been reflecting on my entire wedding experience and how many similarities there are with leading a successful business.

When I got married, I had a big vision for what my wedding day would be like.

For every aspect of the day from what I would wear, to what the wedding site would look like, to the experience guests would have.

Maybe you had a big vision for your wedding or something else that was special to you too?

To achieve this vision, my now-husband and I built our wedding site from the ground up.

We got married in our backyard in a home we had recently purchased that sat on several acres in the woods of CT but that had very little open space - it was all trees and overgrown bramble and weeds.

To create the special spot for our wedding and beyond, we cleared out trees, installed walking paths, created a circle in the middle of the woods for the ceremony, installed ponds and arbors and flowers...

The wedding site came out so beautiful and our wedding ended up being a magical day that far exceeded my expectations and a day that guests still talk about nearly 20 years later.

But it would not have worked out the way it did if we didn't do 2 things:

  1. Start with a clear vision - we knew what we wanted and why it was important
  2. Elevate out of the weeds to see the forest to know where to focus

And I mean that literally, not only as an idiom.

We actually got a drone and flew it above the trees and used that perspective to see what was possible and to create our plan to get there. 🙂

Then we got to work clearing out trees, bramble and weeds, moving rocks, building walking paths and ponds, planting flowers, etc.

We took action on our vision and plan, and we enlisted others to help us bring it to life.

As we were building out our vision, we continuously paused to take the drone back up above the trees to see how we were progressing so we could pivot when needed.

If we just started cutting down trees and digging holes, we may have ended up with something better than what we started with...

But we never could have created the beautifully interconnected and strategically architected wedding site that we both envisioned.


The same is true in our businesses. Let's break it down.

  • You want to start with a clear vision for what you want and why it's important to you.
  • Then you want to elevate out of the weeds so you can see the big picture and how all the parts and pieces of your business interconnect together so you can create a simple and clear plan forward.
  • You want to eliminate all the things in your way so you have the space to create what you want, or as Steve Jobs said in one of his interviews - "get rid of the bramble and the brush so you can shine".
  • Then you want to enlist others to help you bring your vision and plans to life.
  • Along the way, you want to continuously pause to assess how you are progressing so you can double down on what's working and pivot when needed.
  • And you want to celebrate the amazing business you have built, grown, and scaled along with all of the incredible milestones achieved along the way.

Let's take it one step further.

While my wedding itself was an incredible day, when I think back to getting married, what I remember most and what I loved the most was actually the entire adventure leading up to that day.

The planning, the problem solving, the collaborations, the actual work to take an idea we had in our heads and turn it into something real and impactful.

It was a lot of hard work, with plenty of things that didn't go the way we expected (like the time I accidentally lit my back on fire with a leaf blower - don't ask :D)...

But it was so much fun, filled with lots of laughs and so many great and unforgettable memories.

This is what our business journey should be like.

Sure, it's a lot of work. And there are times that are stressful and when nothing seems to go according to plan.

But overall, I believe scaling a business should be one of the most exciting and exhilarating adventures of our life.

It is nothing short of magical that we can take a vision and idea we have in our heads and turn it into something real.

Something that helps others and makes an impact, and that provides financial success for us.

Something that enables us to live our Rich Fulfilled Life™.

Entrepreneurs are the dream chasers and magic makers who change the world.


If it has been a while since you took a pause to appreciate this incredible journey you chose to embark on as a business owner, I hope you will create the space to do so.

Whether this is your 3rd year in business or your 30th, there is so much to celebrate and so many exciting things ahead to look forward to, regardless of where things are right now!

What is something you are celebrating in your business journey?  I'd love to hear in the comments below.

by Crista Grasso

Crista Grasso is the go-to strategic planning expert for leading global businesses and online entrepreneurs when they want to scale.  Known as the "Business Optimizer", Crista has the ability to quickly cut through noise and focus on optimizing the core things that will make the biggest impact to scale a business simply and sustainably. She specializes in helping businesses gain clarity on the most important things that will drive maximum value for their clients and maximum profits for their business.  She is the creator of the Lean Out Method, 90 Day Lean Out Planner, and host of the Lean Out Your Business Podcast


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