How to Transition from Corporate to Entrepreneur

Brittany Eshelman
September 29, 2021

Have you ever thought about leaving your corporate job? The data shows that you’re not alone. One report from Microsoft revealed that 40% of the global workforce is considering leaving their job in 2021. People leave jobs for a variety of personal, professional, and financial reasons. While some look to escape burnout and stress, others seek to develop new skills, test out a different industry, or make more money. 

Regardless of the reason for leaving a job, the transition process can be a stressful experience. This is especially true for anyone looking to move away from a corporate career towards something more entrepreneurial, whether you’re looking to work at a startup or start your own company.  

Bamboo is dedicated to supporting the entrepreneurial ecosystem by offering flexible workspace, networking and community events to engage industry leaders, and years of relationship building with accelerators, investors, and mentors. We have several entrepreneurs within our community who have made the transition from corporate to entrepreneur. 

Get Involved with the Company’s Innovation Branch 

Christina Fair is the Founder of Fair Ventures, offering corporate team building events and leadership development retreats. Fair comes from a corporate background and started her career in the sales department at Quicken Loans.


After 10 years in the banking world, she transitioned to the Mousetrap Team within Quicken Loans. The Mousetrap Team is responsible for internal business consulting and serves as the innovation and culture hub of the company. 

Her experience in the innovation hub gave her visibility to some of the emerging startups while she gained the skills and knowledge to successfully navigate startup environments. This role also provided networking opportunities which facilitated her transition. 

Working on the Mousetrap Team, Fair was asked to help build an internet company, Rocket Fiber. She unlocked doors for them and when they received funding, she joined the Rocket Fiber team full time. Leaving Quicken Loans wasn’t initially part of the plan, but the opportunity to work with the founding team was too good to turn down. Fair served as the Vice President of Client Experience for 7 years before the company sold in April 2020. 


Take Advantage of Opportunities for Training and Advancement

One unique benefit for those coming from a corporate background is the opportunity to receive and apply formal employee training. This is especially beneficial for those who are just starting out or looking to pivot their career.

Reflecting on her experience, Fair identifies the benefits of starting her career in a corporate setting. The formal internal training that she received proved beneficial for Fair who did not come from a banking background. She was afforded opportunities because she earned it with work, effort, and knowledge from growing up in the company. 

Identify Ways to Leverage Industry Knowledge and Transferable Skills

You aren’t starting from scratch, even if you are looking to make a career pivot from corporate. Identify opportunities to address an existing problem or find ways to build expertise from your experiences. 

Fair’s corporate experience provided the opportunity to learn about how company culture is constantly reinvented as a company grows, an experience that would be hard to replicate in a startup environment. Today, she is able to apply her learnings from her past experiences to help young entrepreneurs scale and grow their company culture.

Take Time to Reflect on the Type of Leader You Want to Be

Anyone who is looking to take the leap into entrepreneurship will find it beneficial to develop strong leadership skills and identify a leadership style that works for them. 

Fair reflects on the unique experience of being the only woman in leadership, a daunting experience at first. Once she was promoted to the Vice President role, she had to build trust among the other executive leaders. At the time, she had no idea who she was and the type of leader she wanted to be. She faced pressure to be a more assertive and aggressive leader. Her husband thought otherwise. 

“Everyone I know follows you because you are not that person. They will follow you anywhere and do anything you ask because they trust you. Why would you want to change that core piece of who you are?”    

Fair realized that she could be both a kind and respectful leader while delivering direct feedback when needed. She could show up exactly as she wanted to be. She just needed to take the time to figure out who she was because all she had done was work.

     “If I could go back in time, I would have spent as much time (if not more) focused on who I was as a human and growing myself as a person than I did in my career”    

Fair emphasizes the value of seeking out mentorship outside of the company. She found that actively building strong female relationships and having a community to lean on in hard times was invaluable to her growth. Investing time, effort, and energy into these relationships pays dividends.  

Taking Time to Figure Out if You Want to be an Entrepreneur

One of the biggest advantages of taking a gradual approach is that it gives you the opportunity to test the waters before taking the plunge. 

Rocket Fiber’s acquisition marked a pivotal point in Fair’s career. She quickly realized that she didn’t want to return to her corporate career, the thought of doing so created a visceral response. Fair loved the speed of execution, the ability to see rapid growth, the lack of bureaucracy, and the autonomy. She discovered that working in a startup environment drew on her strengths as an executor. 

While this speed and execution mentality fit with Fair’s personality, it isn’t the best environment for everyone. Working with the Innovation Team and Rocket Fiber gave her the chance to test it out before starting her own venture. 

After 20 years of building a corporate career, Rocket Fiber’s acquisition presented the opportunity for Fair to pursue her own endeavors, and thus Fair Ventures was born.  

Prepare for the Challenges of the Transition

Pop culture and the media can romanticize the startup lifestyle. One thing that is often under-discussed is the loneliness and volatility that accompanies the independence and autonomy of running a company. 

For Fair, who finds motivation in helping others and building community, the hardest part of the transition was the loss of her coworkers who had formed a sense of family. Moving into her office at Bamboo helped Fair to find the same sense of community that she had been missing. She was in an environment where she could meet new people and bounce ideas off of others while having the privacy to get her own work done when needed. 

When Fair launched her website, members of the community provided a fresh set of eyes, offering feedback. When she was struggling with social media, one Bamboo member shared social media strategies and offered to help rewrite some of her content. 

“People would pay thousands of dollars for that... for that thing that she just did for me on a random Sunday while she was sitting on her couch”    

It takes a lot of energy and discipline to build a company. Fair appreciates the vibrant energy that working in downtown Royal Oak brings, a welcomed change from sitting home alone. When nobody is forcing you to do anything, it is important to find ways to hold yourself accountable, to just keep making a bit of progress everyday. 



While the unpredictability of starting a company is inevitable, Fair reminds herself that she is building something for her family’s future. Starting her own company has given her absolute freedom in the choices she makes, from the clients she takes to the marketing direction, the success is a direct reflection of her work. 

For Fair, each transition brought its own set of challenges, from developing her own leadership style as she transitioned to the innovation branch of a corporation to building a community as a solo founder. She has cultivated her own group of executive level women from different backgrounds who meet once a month to provide each other with support and expertise. She also recently joined the Detroit Executive Association and has met a great group of people there.