Advice to entrepreneurs who leave corporate life: Expect to get out of your comfort zone

Article originally published in the Philadelphia Business Journal on June 20, 2016

There are many routes to becoming an entrepreneur. The news media often focuses on millennials and the challenges they face and overcome as they start their businesses. Another path to entrepreneurship can come after years of life and work experience, bringing with it a different set of challenges and rewards.

Lisa Lemire is an entrepreneur who started her business after climbing the ladder in Corporate America. After a 20 year career centered around consumer beverage products at Green Mountain Coffee, Ocean Spray, PepsiCo and Aramark, Lemire welcomed a chance to do her own thing. She became a mid-career entrepreneur, founding Kamini Bay Asset Management, a company that invests funds raised from individual investors to buy distressed residential mortgages.

She and her husband were looking for sources of passive income, a “check in the mail” approach where the assets she owned deliver income every month. Lemire’s husband, Raymond was buying homes, rehabbing them when necessary and renting the homes to tenants, creating a passive stream of income.

Lemire’s business buys mortgage debt that people have stopped making payments on. Lemire explained, “After purchasing the mortgage at a discount from the bank or hedge fund that owns it, we are able to work out a payment schedule with the homeowner that they can afford. We’re always trying to get to the monthly number that they can pay without hardship so they don’t default again. Depending on the situation, we often end up with a lower monthly payment than the homeowner had originally, but one that also provides a return to the company’s investors.”

I asked Lemire, based on her experience, if she could provide any advice to individuals who yearn to become mid-career entrepreneurs. Lemire shared her insights on the following areas:

Lemire said, “Having big company thinking, training and experience in Corporate America – gold standard practices, as well as being around people who were extraordinarily capable, intelligent and competent – has stood me in good stead.”

Entrepreneurs coming out of a corporate career have had hands-on experience, often with years spent hiring people, developing and implementing strategies or running functional areas such as sales or human resources, and learning from the risks they took and the mistakes they made.

Just as important, they often have an established, well-regarded reputation and a network of valuable contacts that can serve as the foundation of a client base for their new business. It is important that all entrepreneurs, regardless of age or level of experience, have seasoned advisors who can provide guidance and mentoring.

… but there are some challenges

It’s often a difficult transition for mid-career entrepreneurs to get out of their comfort zone, try a new way of doing things, take a risk and get something accomplished, as opposed to young entrepreneurs, who don’t yet think that something can’t be done and who find an innovative way to do it. Without taking risks, nothing really gets achieved.

Lemire shared that she has a quote on her desk: “Life Begins at the End of Your Comfort Zone.” It reminds her every day to get comfortable with being uncomfortable.

In a corporate environment, the organization’s goals flow down to you from the chain of command. As CEO of your company, you set the goals. Learning to be your own boss, to be accountable to yourself and “kicking yourself in the butt,” as Lemire put it, may require some creative techniques. What worked for her: checking in with a trusted friend every day for five minutes on how she did on her list of daily goals. “Saying what I was going to do publicly was a big motivator to do it,” said Lemire.

You need a plan to overcome the biggest obstacle to becoming a mid-career entrepreneur: the uncertainty of putting your family’s finances at risk.

“I know many people in their 40s who would like to leave Corporate America and do something on their own, but can’t figure out how to manage without their salary,” said Lemire. “It may take a few years of planning to get there – to save enough (which may require reworking household expenses), to invest in passive income sources that can replace some of the lost income, or have a spouse go back to work.” Not easy.

But, as Lemire also pointed out, “since no job is really safe in Corporate America any more, it feels good to have a Plan B in case you end up without the salary anyway.”

Of course, there are ways to position yourself to be less likely to be “outplaced.” When working for a company, think like an entrepreneur. Embrace continuous improvement. Be sure you differentiate yourself by doing things that are innovative and will benefit the growth and profitability of your company.

This is how you will build your resume to get that next job. You are only as safe as you are essential to your company, or to the next company you want to work for. The riskiest thing you can do is not advance within your company or your profession, or advance slower than your peers. You risk getting left by the wayside as others build skills and a track record of accomplishments that surpass yours.

Lemire shared how she feels when an adverse event occurs in her business. She said, “All entrepreneurs need an inner fortitude to get over rough spots and see things through that don’t go right. Before becoming an entrepreneur, be sure you have that inner fortitude.”

I asked Lemire what keeps her up at night. She said, “I feel a huge responsibility to my company’s investors to invest their funds well.” This commitment Lemire has to those who trust her with their money is an important value. It is a value that all business people should hold dear.

Quoting founding dean Donna Marie De Carolis of Drexel University’s Close School of Entrepreneurship, “Being an entrepreneur is about taking initiative, being flexible, taking calculated risks [and] knowing how to dream and do.” Whether you work in a large corporation or in a small startup, take De Carolis’ advice, and think like an entrepreneur.

Stan Silverman is the founder and CEO of Silverman Leadership. He is a writer, speaker and advisor to C-suite executives on business issues and on cultivating a leadership culture within their organizations. Stan is Vice Chairman of the Board of Drexel University and a director of Friends Select School and Faith in the Future. He is the former President and CEO of PQ Corporation. Follow: @StanSilverman. Connect: Website:

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