09 | 5 Mistakes I've Made Along the Way

Apr 28, 2022

In this episode of The Digital Business Evolution Podcast, Jess shares with us a value-filled exchange that outlines the five mistakes– that are really just lessons– that have shaped how her business runs to this day. The evolution that Jess’s own business has undergone with these lessons can serve as a beacon for other entrepreneurs to look to– to gain confidence and validation, that even though these obstacles have presented themselves, it is something to grow through rather than just go through.

Jess dives into the very first lesson she learns and talks about the need to hire slow and fire fast rather than hiring reactively and firing out of fear which causes us to wait to avoid the inevitable confrontation. As entrepreneurs, we also have a tendency to put our business first which leads to the second lesson Jess gives us. It is okay to put your own life first rather than build your life around your business. For most entrepreneurs, this is the reason we go into business in the first place, yet how quickly we forget and get bogged down in doing just the opposite which can cause many to burn out.

Jess delivers the next lesson to keep our relationship with clients in mind when learning to “sell the island rather than selling the vehicle.” Jess explains that when interacting with clients, keep their intended destination in mind instead of trying to sell your product. 

The final two lessons are the most intrinsic in value when it comes to being an entrepreneur. Don’t get distracted by shiny objects. While this could mean a pivot in your business, Jess contributes that this could also mean getting distracted by comparing ourselves to others. This leads into the final conversation over which entrepreneurs often feel they need to have everything figured out. There is no need to put the immense pressure on ourselves that this mentality can cause– we are not in the “Sororities or Fraternities of Suffering” and can let our egos get out of the way so our businesses can evolve and flourish. 

As always, cheers to your evolution! 

Episode Quotes

  • “I think mistakes are lessons. I think everything we go through, we grow through.” –Jessica DeRose
  • “My business is still a job, but I get to build my life first.” –Jessica DeRose


Key Timestamps

  • [0:46] – Introduction of today’s episode;
  • [1:34] – The start of Jess’s entrepreneurial journey;
  • [2:09] – Accidental entrepreneurship & side hustles;
  • [3:08] – Mistakes are actually just lessons;
  • [4:35] – Lesson 1: Hiring too fast and firing too slow;
  • [7:34] – Outsourcing things that shouldn’t be outsourced;
  • [11:06] – Lesson 2: Building my life around my business and not my business around my life;
  • [17:51] – Lesson 3: Selling the airplane and not the island;
  • [19:14] – Jess dives deeper into selling the vehicle vs. selling the island;
  • [23:38] – Lesson 4: Distracted by shiny objects
  • [30:00] – Lesson 5: Thinking I needed to have everything figured out;
  • [32:28] – Don’t be part of the Sorority of Suffering;
  • [36:25] – Ego is your biggest overhead;
  • [37:47] – It’s ‘Come with me,’ not ‘Look at me’;
  • [38:39] – Recap of the 5 Mistakes/Lessons 


Episode Resources


About Jessica DeRose

Jessica DeRose is an entrepreneur and business mentor, who helps coaches build profitable online businesses. After quitting her 8-year career as an elementary school teacher and creating a multiple 7-figure business herself, Jessica is here to unlock doors you didn’t even know existed.


Connect with Jessica

Instagram: @iamjessicaderose

TikTok: @iamjessicaderose