The Hidden Lessons in the Twists and Turns of the Entrepreneurial Journey

business growth Apr 14, 2022

Did you always know you would be doing what you are doing now in your business? Or when you look back on your entrepreneurial journey, was it full of twists of turns that led you to where you are today?

My journey was definitely a windy road, and as I have been in a state of deep introspection lately, I have been really enjoying looking back at all of the things I thought I wanted to be and do.

I can see now how every one of those paths led me to being the lean business strategist and consultant that I am today.  But I definitely didn't see it at the time.

One of the many things I wanted to be was a photographer, and that was even what I majored in for the 1st part of college. 

I used to photograph and interview musicians and models and always pictured myself as a photojournalist with my own magazine or as a photographer for an amazing bohemian brand traveling the world taking photos in exotic locations.

I did both of those things for a while, launching my own magazine and launching my jewelry brand where I styled some epic photoshoots.

There was so much I loved about being a photographer. But over time, I realized it wasn't what I was meant to do.

I realized that what I loved most about photography wasn't actually taking the photos... it was the visioning, the planning, the styling, the curating to visually communicate the desired message.

My photos appeared great because of all the behind the scenes planning and prep I did.  But the reality is that I wasn't all that great of a photographer technically. While I was a master at framing and composition - the creative aspects, I was far from a master at f-stops and shutter speed and all the technical aspects.

For every 1 "amazing" picture that people saw, there were 100 others I took that were utter garbage and completely unusable.

I was working harder not smarter every time I picked up the camera and I knew that wasn't sustainable. I either had to really learn to master the technical components (which did not seem exciting to me) or move on.

So I stepped into what I loved most - the strategy, planning, styling, & creative elements of a photoshoot and let someone else be the person behind the camera.  I become the visionary and leader and found someone else to capture the photos.

It was hard to let that go at first but absolutely the right decision.

It taught me to:

  • Focus on what I do best and let others do what they do best - the art of delegation and team.
  • Not be afraid to let go of and reimagine things, including my identity - the art of leaning out and leveling up.
  • Always look for sustainable solutions and ways to work smarter not harder - if it consistently feels draining and like way too much work, it's not the right path.
  • Look for the clues every experience provides - vision, strategy, planning, creativity, team - I'm sure you can see the parallels with what I do now. ;)

It also taught me the importance of curation, leadership, and strategic partnerships.

Realizing I wasn't meant to be a photographer actually made me a better business strategist and consultant and paved the path for me to step further into that role.

How about you?  Did you envision a different path that actually led you to what you do today?

I highly recommend that you carve out a few minutes to reflect back on the twists and turns that brought you to where you are today.  Not only is it kind of fun to piece everything together to see how each experience influenced what you do now, it is also a great reminder the next time you are going through a period of major change or reimagining that it is all just part of the entrepreneurial journey.



When you are ready to accelerate making your big bold vision a reality, here are 2 ways I can support you:

  1. Want to spend a full day together deep diving into your scalable signature offer or developing your strategic plan for your next big bold business move? Learn more about working together privately in a VIP Strategy Day here.

  2. Looking to scale your business faster? Our Simplify to Scale Business Accelerator helps you eliminate unnecessary complexity and build a business that runs itself through simple systems and a rockstar team so you can step into your next level of visionary leadership and dramatically increase your impact and profitability. Learn more and apply to join our next cohort here.


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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