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How to Move Forward When You Want to Quit Your Business

Entrepreneurs share their tips for staying motivated when you're feeling frustrated

By Emelie Smith Calbick and Betty Wong

Every entrepreneur has experienced it.  Those days when nothing seems to be going right. Those frustrating times when you can't see a path to success ahead. Before you throw in the towel and give up, learn from these entrepreneurs on how they push through the tough times.

An older adult standing on the floor of the New York Stock Exchange. Next Avenue, entrepreneur, business inspiration
Tanya Van Court  |  Credit: NYSE

In October, our company Stage2Startups, an organization that helps older, experienced workers start their own business, invited over 30 "second stage" founders to speak at our first Founders Over 40 Conference.

"Don't get lost in the day-to-day of your business and lose sight of your mission."

Speakers came from all backgrounds and industries; they either started their companies from scratch or bought and built a company; and, they started both for-profit and nonprofit organizations.

While every entrepreneur's journey is unique, we learned that everyone who sets out to start their own business will experience those moments when success does not look possible.

Here is some advice on how these business founders stayed motivated:

Have a Plan

One of the best ways to prevent feeling discouraged as you build your business is to have a solid plan.

Richard Russo, CEO of Endomedix, a biotechnology firm based in Montclair, N.J., notes that when entrepreneurs focus only on the end goal, they can lose sight of what needs to be done in the short term to reach that goal.

"When your goal is so far away, it is hard to see the light at the end of the tunnel and you can feel like you are not getting anywhere," says Russo, who counsels every founder to create a plan with concrete milestones and the steps needed to achieve each milestone.

"Now, when you achieve a milestone, you can feel good about yourself and look back on what you achieved. In addition, you can now communicate your success to others, which also builds your confidence."

Remember Your "Why"

Even with a plan in place, it is never a smooth path to achieving your goal.

Gary Portuesi, founder of the luxury travel business, Authentic Explorations, based in New York City, talked about how easy it is to get overwhelmed by the general chaos of the daily tasks of building a business.

A woman wearing colorful clothing standing next to dress forms. Next Avenue, entrepreneur, business inspiration
Ngozi Okaro  |  Credit: Carolina Isabel Salazar

He advises, "Don't get lost in the day-to-day of your business and lose sight of your mission. Take a deep breath, and remember to keep looking at the longer term view."

Ngozi Okaro, the New York City-based founder of the nonprofit Custom Collaborative, which offers training to low and no-income women and immigrant women in the fashion industry, planned out where she wanted to be in 3, 5 and 10 years. Then, when frustrations built or nothing seemed to be going right, she could always look to the future. 

"When I am in frustrating moments, I step back and remember that this particular moment is not the moment I am living for," says Okaro. "I remind myself that I am working for the big moments when I know I am making a transformational impact on women's lives. This helps me get over the short- term frustration and refocus on my bigger mission."

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Build Your Support Group

Being a solopreneur does not mean you have to do it alone when you hit a roadblock. Our entrepreneurs cautioned against becoming isolated and instead take the time to find people with the skills and willingness to help. These people can serve as sounding boards, brainstorm solutions, and help open doors. 

An older adult wearing a grey suit speaking on a stage. Next Avenue, entrepreneur, business inspiration
James Rosseau, Sr.  |  Credit: LegalShield

"The ability to pick up a phone and ask some people for help is invaluable," says James Rosseau, Sr., founder of The Corelink Solution, a Wilmington, Del. nonprofit focused on revitalizing communities through programs that help people realize their potential.

Rousseau suggests finding people on LinkedIn with the skills and knowledge you need and do a "cold call" introduction explaining why you want to connect with them.

"You would be surprised at how many people want to help," he says.

New York resident Deb Boulanger, founder of The Launch Lab, a mentoring program for women entrepreneurs, also recommends building a community of people you trust because "the last thing you want to do is struggle alone." 

However, she counseled that you must build your support group with the right people.

"Friends can't help you because they don't have the expertise in what you are trying to build.  You need people who are working in the same space as you and who have experienced the same challenges. These people can commiserate with you, share their experiences, and help you work through the moment," says Boulanger.

Keep Your Grit

An older adult speaking in front of a business meeting. Next Avenue, entrepreneur, business inspiration
Deb Boulanger  |  Credit: Lauren Kress

Educators talk about the importance of grit for children to succeed. The same is true for entrepreneurs. A consistent theme among our entrepreneurs was the importance of not letting short-term challenges or naysayers derail their long term goals.

But perseverance does not mean beating your head against the wall. Instead, step back and reevaluate.

Tanya Van Court, who founded Goalsetter, a family savings and spending app, says, "Treat any barrier as an obstacle. A barrier means that you can never get from point A to point B, but with an obstacle you can figure out how to go around, under or over it."

Jeanne Pinder, founder of ClearHealthCosts, talked about what it was like launching a tech startup, focused on transparency in health care pricing, as a 55-year-old woman. 

"I encountered a lot of naysaying - I was too old to start a company or I couldn't start a tech startup because I was a woman. But you have to turn that negativity into something good. I became motivated every time someone said I couldn't do something. I didn't take no for an answer and I didn't give up," Pinder says.

Editor’s note: This article is part of America's Entrepreneurs, a Next Avenue initiative made possible by the Richard M. Schulze Family Foundation and EIX, the Entrepreneur Innovation Exchange.

Contributor Emelie Smith Calbick
Emelie Smith Calbick 



Emelie Smith Calbick built her career in financial services, holding a variety of senior level marketing and strategy positions at American Express, Citigroup and JP Morgan Chase. Emelie is co-founder of Stage2Startups, an organization that supports Baby Boomer and Gen X professionals who are thinking about, or who have already left, their career path to successfully found and grow their own business.
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Contributor Betty Wong
Betty Wong 



Betty Wong is a serial entrepreneur, new products marketer, educator, consultant, mentor and coach. Her clients, employers and board assignments have included startups (including her own), and Fortune 500 level companies (Colgate-Palmolive, Mars, Johnson&Johnson, Honeywell, NYTimes) and others. Betty founded Stage2Startups in 2017 when she realized there were no organizations helping founders over 40.
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