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  • Jennifer Gibbs

Bold Career Moves – from Corporate Executive to Entrepreneur

Updated: Mar 30


You know the saying – people don’t leave bad jobs; they leave bad bosses? I hate that saying. Admittedly, I am slightly offended by it, having managed people for over 20 years, many of whom chose to move onto other roles in part because I was a good boss. Mostly, I hate the saying because it isn’t useful. It tries to simplify a decision that is both deeply personal and highly nuanced.


Do people leave jobs because they think their boss is terrible – of course! Your relationship with your boss matters. However, a whole lot of other things matter as well, not the least of which is the answer to this question:

What do you really WANT to experience next and is that available in this job, company or industry?

This is the question I’ve asked myself many times throughout my 25-year career, resulting in me moving into new roles nearly every 3 years. After a very successful 17 years, including 5 promotions within the same large tech company, I started to realize the company itself could no longer offer what I wanted – a totally new perspective in a totally different culture.


It took me 2 years to muster up enough clarity and confidence to start to explore what opportunities might be available to me outside the company. This was a miserable but also critical learning experience for me. (If only I had hired a coach back then!) After several months of finally reaching out to my network, I made a carefully orchestrated move out of tech and into banking – changing companies and industries but still leveraging my technology and leadership experience in an executive role in data and analytics. This bold move helped me to appreciate how marketable my skills and experiences were “on the outside”. This came in very handy in 2019 when I found myself realizing again that the company I was working for may no longer offer what I wanted – was I ready to “retire” from corporate life altogether?


What I wanted came as a whisper at first – I think I want to become a certified career and leadership coach and run my own business. Um, what? That desire was completely unplanned and unexpected and frankly kind of terrifying. On top of that, the job I had was great – great team, great boss, great company, lots of challenges and opportunities to learn and make a difference. Still, I knew I was ready for a new adventure. So, I started doing what I knew how to do best – exploring what other corporate roles were available. I found lots of interesting options inside and outside of my company, but they all just felt “meh” to me. I even went through 7 intense (and valuable) interviews for what I would have previously considered an amazing opportunity. Yet there wasn’t my usual “fired-up” feeling for it. It simply wasn’t the job for me.


That whisper of a desire to run my own company started to get louder and I finally started to pay more attention. While I would say I have always been willing to take risks, I don’t take them without a great degree of thoughtfulness. This felt like a big risk to me. We were a single income family with two kids entering university shortly.

Mostly though, my biggest obstacle was facing this great unknown and trusting myself to figure things out.

My carefully orchestrated move from corporate executive to full-time entrepreneur began with getting my life coach certification from The Life Coach School and incorporating my business Jennifer Gibbs Coaching, Inc. in April 2020 “on the side”. Although I had been coaching colleagues for many years, I gained the first of many incredible paying clients that summer. I learned a lot about a lot of things. The most important thing I learned was how much I loved coaching and seeing the impact it was having on my client’s lives. I also loved every aspect of running my business. It was clear to me that there was no other path to explore – entrepreneurship came looking for me and I was ready to embrace it. I laid out a plan to quit my job in 2022 and in February of that year, I officially said farewell to corporate life and hello to full-time entrepreneurship.

Still figuring things out. Here for ALL OF IT.

For those of you looking to make a bold career move, here are 2 powerful beliefs that were critical for me to build and embrace – and these did not come easily – that I think would serve you well regardless of your circumstances.


Belief #1: I am incredibly marketable.

I realized I was not leaving my corporate career “behind”, I was taking every bit of the knowledge, experience, and network I gained along for a new ride. I took stock of all that I had experienced so far in my life and career and the millions of times I overcame obstacles. I decided that I would always have a lot of options to choose from, a lot of paths available for me to explore. Entrepreneurship was simply the next best path for me right now.

Job “security” is not something a company offers. This security is always with us in the form of our unique skills, beliefs and experience.

Belief #2: I can create as much money as I want because I can create value.

For me, releasing the “golden handcuffs” was no joke. At minimum, I wanted to be sure we could still pay our bills. Moreso than that though, alongside purpose and passion - making a lot of money matters to me. I got to work “doing the math” on our financial position and options. I also “did the math” on the money I believed I could create from the value I was willing and able to offer. My geeked up spreadsheet looked reasonable and promising. However, I think it was the 3-month unpaid leave of absence I took in 2021 that not only allowed me to “practice” using money to invest in me, it gave me the time and mental space to brainstorm all the value I could create for my clients.

The thing about beliefs is that they truly are the driving force of our results.

The more awareness and curiosity we bring to our beliefs, the more empowered we are to decide which ones are worth keeping. Beliefs that serve us deserve our care and attention. They get tested many times as we head into a new bold adventure. Believing is an action that requires practice. This practice starts with awareness and honesty.


Here are some bold questions to help you get started on your next bold move…

  • What do you believe about what possibilities are available to you?

  • What do you believe about your ability to create value for yourself and others?

  • What do you believe about your ability to take risks and overcome obstacles?

  • Are these beliefs helping or hindering the results you want in your life?


If you need help with your next bold move, book a free consult with me via my website https://www.jennifergibbscoaching.com. I’d love to coach you forward.


#makeboldmoves #liveyourdreams #goforit #careergoals #coaching #leadership #entrepreneurship #keepbeingamazing #justbeyou #ownyourawesome #womeninleadership #boss

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