How Parents of Entrepreneurs Support Alternative Paths

As a parent, what should you do if your adult child chooses not to take a normal job after finally getting a diploma? Sure, the job market is tough for new grads, but your friends’ recent graduates are finding jobs. And your child has interviewed for a few jobs you thought would be great.

But what if your child tells you they honestly can’t imagine taking the kind of entry-level job you signed up for back when you graduated? What if you always told them to be practical, but they don’t want to be practical any longer? What should you do?

While researching how parents of entrepreneurs raise their children, I interviewed 70 thriving self-starters who took a different path from most college graduates. They represented a diverse group from a variety of career paths. All had decided not to be practical and instead set out to turn their passion into a career.

Fundamentally each of their parents followed their child’s lead when they deviated from pursuing a traditional job. And the parents’ support as they pursued their passion was crucial to their success.

Let go of your nervousness. Take comfort in these stories of successful entrepreneurs who decided not to go the route of a traditional career, but instead to follow their dreams.


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When Bert Jacobs graduated from college, he and his brother Johnny started selling T-shirts they designed on the streets of Boston. Their friends would ask disapprovingly, “What are you doing with your life?” After a few years, they came up with Jake, a smiling stick figure with “Life Is Good” written underneath. Their T-shirts are now sold in over 4,000 shops across the U.S. and in 30 countries around the world.

Joel Holland was getting ready to graduate from Babson and had a six-figure job offer on Wall Street. He turned it down. All his friends said he was nuts. He moved home with his parents and worked on the company he had started while he was in high school, called Video Blocks, selling stock film footage. Within five years he sold half of it for $10 million. Then he started pursuing his other passion — touring the country in an RV — but he hated staying in crowded RV parks. He bought a small company called Harvest Hosts, providing memberships to stay in farms and wineries in places he had wished to stay. It now has over 2,000 locations. Joel told me, “When you love something, and get to understand every aspect of it, you’ll realize what you can add, and you can make a business of it.”

Paige Mycoskie had always loved art, but after college, she took a traditional job. A few years later, she bought a used sewing machine and told her parents she was quitting her job and moving back to their home in Texas to sew. After a few months, she took the first group of surfing-inspired clothes she’d made to Los Angeles and sold them to Fred Segal, a high-end clothing store. Within three years, she opened her first store, Aviator Nation. She now has 13 stores and is opening more around the world.

Thomas Vu was majoring in bioengineering at the University of California San Diego, but his passion was video games. He was one quarter away from graduation when he had a chance to talk to someone from Electronic Arts who was a guest speaker at his school. Thomas told him about an idea he had for a game, and soon was invited to join the Sim City team as an intern. He dropped out of school and became the lead producer on League of Legends. It now has over 100 million monthly active players around the world. Last year he became executive producer of the breakout Netflix hit series Arcane.

Unjoo Moon’s family was unhappy when she announced she was giving up the law to try to get into film. Then she went on to direct and produce many winning films and music videos. In particular, her film I Am Woman, the Helen Reddy biopic, has enjoyed much critical acclaim.


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Not everyone thrives on risk, is tolerant of uncertainty and is willing to work really hard to turn their passion into a project. But if that’s your child’s dream, tell them to go for it. Let them know they should try doing what they love, not what they think will please their family, or their teachers, or their friends.

Will they all be successful at everything they try? No, not all. Will they hit bumps in the road? Of course. Let your child know it’s all right to fail and that failure is how they will learn and grow.

Naturally, you’re concerned they won’t make enough money to live. But let go of your anxieties about their future. Tell them you know it may be hard, but you want them to pursue their passion, and take a chance on turning their dream into reality. Then take a deep breath and try to be excited for their journey. It could be the start of something great.

Adapted from the book, “Raising an Entrepreneur: How to Help Your Children Achieve Their Dreams – 99 Stories from Families Who Did.”


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