My Entrepreneur Journey: Innovation, Iteration & Failure

The last year has been one heck of a ride. 

I was reminded of this the other day when a keynote speaker mentioned this oft-repeated (and true) observation about innovation: successful innovation requires that we love solving the problem and not be in love with the solution. Why? The emotional attachment to a solution prevents decision makers from pivoting away from bad solutions (failing fast) and remaining focused on solving the problem (iterating and/or innovating).

Failing fast & iterating are crucial elements corporate innovation.

It is no different for entrepreneurs. Just like our corporate counterparts, the path for an entrepreneur is rarely reflected in the end product or service everyone sees. The path to get there has so many pivots it looks like a Family Circus cartoon.

For that reason, I am telling you my story. Pivots abound!

After +7 years modifying outdated content from the leadership & management courses I would take, I grew frustrated. Days were wasted in courses that clearly had a few hours of usable content, at best. Content which rarely addressed actual challenges facing people managers.

I saw good companies repeat the same mistakes: over-promoting, unable to truly count on their leadership to step up and seeing change initiatives fail (managers are the #1 point of failure for successful change management adoption).  Organizations will not be successful if their people practices result in losing the best and keeping the rest. Finally, I stopped looking around for someone else to design this for me and dove in myself.

Getting started.

The problem I wanted to solve was clearly defined, and my natural inclination for a solution was to be an onsite consultant. The original lesson plans I had designed for my own teams in the past were gathered together and broken out into modules that I could use interchangeably based on the clients' needs. I was ready to go, started a website, ordered the business cards and got busy meeting & greeting. 

Then came the first pivot.

glendalynn dixon recovery

A few months after deciding to pursue my own consulting business, I found out I was to undergo a surgery which meant I would be housebound for 8 – 12 weeks, and in a cast for many weeks following that, in the middle of winter. I felt defeated. How on earth was I going to build a consultancy when I was confined to one floor of my house? I wasn’t going to be able to make much headway in that space for a few months. If I couldn’t go onsite then I would move online. Necessity is the mother of invention after all!

Pivot #2 followed quickly. 

After reviewing all of the original lessons I had created, I decided upon five that made the most sense as the foundation for an online management training program. Decisions made, I underwent surgery at the beginning of December with a plan for constructing the beta version of my program by the end of January. It is laughable now, but I had greatly underestimated what my recovery would look like. Not only that, the mental wellness challenges faced from the social isolation were shocking. I grew depressed and was in my own head too much.

Pivot #3 was a direct result of this over internalization. 

I became sensitive to how much I was “out there” in the public sphere and opted to create the program using a new company name, one that masked my involvement. You might think I was overreacting, (I’m not exactly Oprah famous), and yet this is a shared experience with many people who start their own business. It is all relative. The decision resulted in me designing new branding, creating all of the online lessons and setting out to beta test the course. Turns out the beta test was of my ability to build an online course. What a learning curve. 

For those of you who have never had to listen to your own recorded voice for any length of time, let me set the record straight: it is a form of hell on earth.

Pivot the 4th undid everything from in the last step. (Fail fast). 

The feedback was resounding: separating ‘me’ from the online program made no sense. It was driven by my experience. My story led me to this. It was my voice, my original content and 100% my design. I had to start over – discarding all of the work from pivot three. 

glendalynn dixon entrepreneur journey

I dissolved the new company and combined my personal brand with the online management training program. Was it a lot of effort to re-brand the content, redesign the videos and re-record all of the voice overs? *sighs* Yes. But it turns out I LOVED THIS! The experience of creating became enjoyable. Ideas for future programs just started flowing. That’s when I stopped feeling like I was pushing water uphill.

My image, my no-nonsense delivery, my voice. As scary as it seemed, it finally clicked. The personal connection was what clients related to. And because they were starting to know me through my articles or videos, the connection to the online course was made even easier.

How does this tie back to successful innovation? 

I wasn’t married to the initial solution (onsite consulting) at the expense of my passion for solving the problem (building strong management teams). When it made sense to iterate, I did. When it made sense to go right back to the drawing board, I did. I’m not going to say that it wasn’t emotionally crushing at times. I absolutely felt like a failure more than once. Driven by the desire to solve a real problem, I kept moving towards the next solution. 

That is our challenge – separating a failed solution from feeling like a personal failure.

If you have chosen to create your own path, pursue a side gig or know someone who is, keep this in mind. Go easy on yourself. Love solving the problem. Your next best solution is always a pivot away. 


Glendalynn Dixon guides business transformations focused on culture, leadership & data management. She is an author, speaker and mentor who champions women in technology and uses stories from her wild ride of a life to challenge preconceived notions. Glendalynn developed The Successful People Manager, a no-nonsense online management training program for leaders committed to professional growth and is a featured author sharing her story of finding her voice to create change in Carpe Diem

Learn how Glendalynn can help your business here , contact her directly or follow her on Instagram or LinkedIn .